Grey Dotted Circle in iTunes

Try the following all-purpose steps for dealing with erratic device or sync behaviour. They assume that all of the content you want on the device is in your library ready for restoring. If it isn't see Recover your iTunes library from your iPod or iOS device first. I would also recommend you copy everything out of the camera roll if you haven't already.

1. Backup device. (To iTunes, over USB, with your laptop on power, make sure it doesn't sleep)
2. Restore as a new device. (Restore your iPhone, iPad, or iPod to factory settings - Apple Support)
3. Restore the backup you made earlier.

Use an encrypted backup if you want to preserve passwords, Wi-Fi settings, web history and health data where appropriate. I also suggest syncing with a selection of playlists (unless you're using iCloud Music Library) rather than manually adding content as, if nothing else, the process above is easier to do if you ever have to go through it again.

tt2

I first ensure my iPhone is backed up and the syncing process is complete. While the iPhone is still connected to iTunes, I go to the affected songs on my iPhone and delete them from the playlist by:

1. Pressing and holding the song

2. Selecting "Delete from Library"

3. Then "Delete Song"

After I have deleted all the "greyed circled" songs, I re-sync the phone by pressing the "Sync" button and I watch as the greyed circled songs become checked. I've done this a few times now and there has been no loss in data. I hope this helps.

Did you do step 2? Try changing your sync settings so that no music is actually selected to sync, sync the device, then switch to manual management and delete anything that still remains. Then try syncing a single small playlist to see if that copies over in whole with no dotted tracks.

tt2

Did you ever figure this out? I tried the suggestion by Traveler4Hire here in this thread and it worked. The only problem is that since there were numerous songs with grey circles spread throughout my playlists, when I synced everything afterwards, it created a duplicate of all my playlists, so that took some time to delete and resync again. So far, so good though. This didn't happen to me until this last update this week. We'll see if it makes it the next time there's an update.

I'm feeling like this is a stupid question, but if you deleted the songs from your phone and presumably can't see them any longer, how can you "watch as the grey circled songs become checked"?

By looking at the display of the contents of the device when it is connected to iTunes.

tt2

This worked a treat.

What do you mean by "Pressing and holding the song"? I'm in Windows 10, and I can click or right-click the song but I see no option to Delete the song from anywhere.

"pressing and holding" on the iPhone, not in Windows